The Stereochemistry of P-N Bond Cleavage in the Staudinger -Wittig-type Reaction of 2-Anilido-3,4-dimethyl-5-phenyl-l,3,2-oxazaphospholidine-2-thiones
نویسندگان
چکیده
Krystyna Lesiak and Wojciech J. Stec Polish Academy of Sciences, Centre of Molecular and Macromolecular Studies, 90-362 Lodz, Boczna 5, Poland Z. Naturforsch. 33b, 782-785 (1978); received March 28, 1978 1,3,2-Oxazaphospholidines, (—)Ephedrine, Thioanilides, Thioesters, Stereochemistry Both isomers of 2-anilido-3,4-dimethyl-5-phenyl-l,3,2-oxazaphospholidine-2-thiones (2 a and 2 b) derived from (—)ephedrine were obtained and converted to corresponding 2-thiomethyl derivatives (3 a and 3 b). The Staudinger-Wittig-type reaction of P-N bond cleavage was found to proceed with full retention of configuration at P-atom involved into five-membered ring system.
منابع مشابه
Solvent-free and one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones using ionic liquid N,N-diethyl-N-sulfoethanammonium chloride {[Et3N–SO3H]Cl} as a green catalyst.
In this work, the ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl}, N,N-diethyl-N-sulfoethanammonium chloride was used as a green acidic homogeneous catalyst to synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones as two categories of heterocycles, from aldehyde, dicarbonyl compound and urea or thiourea throughout the one-pot three components cycloc...
متن کاملA Facile and Environmental Friendly Method for C=N Bond Cleavage of Imines Using p-Toluenesulfonic Acid in Solid State
A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. ...
متن کاملReaction mechanism and kinetics of the traceless Staudinger ligation.
The traceless Staudinger ligation enables the formation of an amide bond between a phosphinothioester (or phosphinoester) and an azide without the incorporation of residual atoms. Here, the coupling of peptides by this reaction was characterized in detail. Experiments with [(18)O]H(2)O indicated that the reaction mediated by (diphenylphosphino)methanethiol proceeded by S-->N acyl transfer of th...
متن کاملEthyl 5-methyl-4-oxo-3-phenyl-2-propylamino-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
The title compound, C(19)H(21)N(3)O(3)S, was synthesized via the aza-Wittig reaction of functionalized imino-phospho-rane with phenyl isocyanate under mild conditions. In the mol-ecule, the fused thienopyrimidine ring system is essentially planar, with a maximum deviation of 0.072 (2) Å, and makes a dihedral angle of 60.11 (9)° with the phenyl ring. An intra-molecular C-H⋯O hydrogen bond is pre...
متن کاملEthyl 2-isopropylamino-5-methyl-4-oxo-3-phenyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
The title compound, C(19)H(21)N(3)O(3)S, was synthesized via an aza-Wittig reaction of a functionalized imino-phospho-rane with phenyl isocyanate under mild conditions. In the mol-ecule, the fused thienopyrimidine ring system makes a dihedral angle of 66.30 (11)° with the phenyl ring. An intra-molecular C-H⋯O hydrogen bond occurs. The terminal -OCH(2)CH(3) group is disordered over two sites wit...
متن کامل